The addition of carboxylic hydrazides (e.g., benzoylhydrazide) to the C .dbd. C bond of acrylonitrile was reported by Ebnother et al (Helv. 42, 553 (1959)). The reaction proceeds rapidly, even in the absence of catalysts, and produces N-benzoyl-N'-B-cyanoethylhydrazine in high yields. No disclosure is made of the further reaction of this material to make high molecular weight rubbery, thermoplastic or thermosetting products. Hydrazides are suggested as curing agents for epoxy resins ("Encyclopedia Of Polymer Science And Technology," Vol. 6, 1967, John Wiley & Sons, Inc., page 235). Polyhydrazides have been prepared by reacting hydrazine hydrate with a polyester to provide side chains of hydrazide groups. Linear polyhydrazides have been formed by heating arylene or alkylene diesters with 1,6-dihydrazinohexane (NH.sub.2 NH(CH.sub.2).sub.6 NHNH.sub.2). Still other polyhydrazides have been prepared by reacting a diester, a diacyl dichloride or a dibasic acid with hydrazine or a dihydrazide in solvent ("Encyclopedia Of Polymer Science And Technology," Vol. 11, 1969, John Wiley & Sons, Inc., pages 169-175, 183, 184, and 187).
An object of this invention is to provide novel reaction products of hydrazides and activated unsaturated esters. Another object is to provide novel polymeric reaction products of hydrazides and activated unsaturated ester compounds with or without reactive melamine, urea or phenol-formaldehyde resins, such products being useful as coating materials, adhesives, potting compounds or the like. A further object is to provide such products exhibiting improved impact resistance. Yet another object of this invention is to provide substrates with adherent polymeric coatings of such hydrazide-unsaturated ester reaction products. Still another object is to provide laminates in which the adhesive bonding layers of the laminates together is such a reaction product. These and other objects and advantages of the present invention will become more apparent to those skilled in the art from the following detailed description, the working examples, and the accompanying drawing (Example 3, infra).